Watch: 5 worst defeats of Arsene Wenger's career

Over the last two decades, Arsene Wenger has established himself as one of the best managers in the history of modern football. The 67-year-old, who is the longest-serving manager in Arsenal’s history, has led The Gunners to three Premier league titles and six FA Cups.

Wenger’s 20 years at Arsenal has seen more ups than downs and when he took charge in 1996, he rejuvenated the London club with his style of play.

However, Wenger has failed to lead Arsenal to European glory in spite of the fact that The Gunners have been regulars in the competition. Arsenal even had a 9-year trophy drought which came to an end after their FA Cup triumph in 2014.

The life of a manager is far from comfortable and even though Wenger has done an immaculate job at Arsenal, there were moments when his blushes could not be spared. His Arsenal team has suffered some embarrassing defeats and this piece mentions five of them.

#5 February 8, 2014 – Liverpool 5-1 Arsenal

It was just five, but it could have been more as a rampant Liverpool side demolished Arsenal and was up by four goals inside the first 20 minutes. Arsenal, who went into the fixture top of the Premier League table, were no match for The Reds.

Martin Skrtel got on the end of two Steven Gerrard set-pieces in the first and ninth minute. Raheem Sterling scored the third goal and Philippe Coutinho’s beautiful pass set up Daniel Sturridge for the fourth. Arsenal were shocked and humiliated as they found themselves trailing by four goals at half-time.

Raheem Sterling, who was the man of the match, scored again early in the second half to make it 5-0 to the hosts. Mikel Arteta converted a penalty in the 69th minute after Alex Oxlade-Chamberlain was brought down. It wasn’t even a consolation goal as the day was one to forget for Arsene Wenger and his team.